benzyl(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidine-1-carboxylate

Base Information

• Chemical Name: benzyl(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidine-1-carboxylate
• CAS No.: 1030899-58-1
• Molecular Formula: C₁₄H₁₉NO₃
• Molecular Weight: 249.31
• Mol file: 1030899-58-1.mol

Synonyms:benzyl(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidine-1-carboxylate

Chemical Property of benzyl(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

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MSDS Files:

Useful:

Technology Process of benzyl(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidine-1-carboxylate

There total 1 articles about benzyl(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidine-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylate (1030899-57-0) + methylmagnesium bromide (75-16-1) → benzyl(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidine-1-carboxylate (1030899-58-1)

Guidance literature:

With cerium(III) chloride; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; for 1h; stereoselective reaction;

DOI:10.1016/j.bmcl.2017.03.038

Reference yield:

benzyl(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidine-1-carboxylate (1030899-58-1) → 2-chloro-4-[(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidin-1-yl]benzonitrile (1030899-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 1.5 h / 20 °C

2: lithium carbonate / dimethyl sulfoxide / 18 h / 80 °C

With palladium 10% on activated carbon; hydrogen; lithium carbonate; In methanol; dimethyl sulfoxide;

DOI:10.1016/j.bmcl.2017.03.038

Reference yield:

benzyl(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidine-1-carboxylate (1030899-58-1) → 2-fluoro-4-[(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidin-1-yl]-3-methylbenzonitrile (1030898-85-1)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 1.5 h / 20 °C

2: lithium carbonate / dimethyl sulfoxide / 18 h / 70 - 80 °C

With palladium 10% on activated carbon; hydrogen; lithium carbonate; In methanol; dimethyl sulfoxide;

DOI:10.1016/j.bmcl.2017.03.038

upstream raw materials:

benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylate

methylmagnesium bromide

Downstream raw materials:

2-chloro-4-[(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidin-1-yl]-3-methylbenzonitrile

2-chloro-4-[(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidin-1-yl]benzonitrile

2-fluoro-4-[(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidin-1-yl]-3-methylbenzonitrile